N-benzyl-4-bromobenzimidamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-4-bromobenzimidamide
• 英文别名: N-benzyl-4-bromobenzenecarboximidamide；N'-benzyl-4-bromobenzenecarboximidamide
• 化学式: C₁₄H₁₃BrN₂
• 分子量: 289.175
• InChiKey: LXCHUAHTIQKUEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-bromobenzimidamide 在 氧气 、 copper(l) chloride 作用下， 以 二甲基亚砜 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以76%的产率得到2,4-双(4-溴苯基)-6-苯基-1,3,5-三嗪
  参考文献：
  名称：

  A novel straightforward synthesis of 2,4,6-triaryl-1,3,5-triazines via copper-catalyzed cyclization of N-benzylbenzamidines

  摘要：

  DOI：

  10.1016/j.tetlet.2014.10.091
• 作为产物：
  描述：

  4-溴苯腈 、 苄胺 在 aluminum (III) chloride 作用下， 反应 0.67h， 以78%的产率得到N-benzyl-4-bromobenzimidamide
  参考文献：
  名称：

  通过串联氧化重排和异氰酸酯消除反应，由N取代的Am合成仲酰胺

  摘要：

  在这项工作中，已经描述了将N-取代的idine转化为仲酰胺的有效串联过程。该过程涉及Ñ通过与双衬底的反应-acylurea形成（酰氧基）（苯基）-λ 3 -iodane随后的异氰酸酯的消除。通过与羧酸的配体交换从可商购的二乙酸苯基碘（III）苯乙酸[PhI（OAc）2（PIDA）]获得高碘烷试剂。该ñ预取代的idine底物很容易从容易获得的腈中合成。该方法适用于基于脂族和（杂）芳族胺的仲酰胺合成，包括由位阻酸和胺组成的挑战性酰胺。而且，该方案允许将目标酰胺（基于苯胺）中的空间体积与电子缺乏结合起来。基于涉及羧酸和胺的经典缩合反应，这样的化合物难以有效地合成。总体而言，在脂肪族和（杂）芳族体系中，合成方案都能将腈转化为仲酰胺。

  DOI：

  10.1002/adsc.201400648

文献信息

• Chemoselective synthesis of 5,4′-imidazolinyl spirobarbiturates <i>via</i> NBS-promoted cyclization of unsaturated barbiturates and amidines
  作者：Hui Xu、Rong-Lu Huang、Zhu Shu、Ran Hong、Ze Zhang

  DOI：10.1039/d1ob00508a

  日期：——

  A selective cyclization of unsaturated barbiturates and amidines promoted by N-bromosuccinimide has been successfully developed to afford a vast variety of 5,4′-imidazolinyl spirobarbiturates in moderate to good yields. The present protocol features broad substrate scope, facile work-up procedure and mild reaction conditions, providing a novel strategy for the highly selective and efficient construction

  由N-溴代琥珀酰亚胺促进的不饱和巴比妥酸盐和脒的选择性环化已成功开发，以中等至良好的收率提供种类繁多的 5,4'-咪唑啉螺巴比妥酸盐。本协议具有广泛的底物范围、简便的后处理程序和温和的反应条件，为结构多样的螺咪唑啉的高选择性和高效构建提供了一种新策略。
• IMIDAZOLE BASED LXR MODULATORS
  申请人：Busch Brett B.

  公开号：US20100075964A1

  公开（公告）日：2010-03-25

  Compounds of the invention, such as compounds of Formulae IIa, IIb, IIc or IId, and pharmaceutically acceptable salts, isomers, and prodrugs thereof, are useful as modulators of the activity of liver X receptors, where R 1 , R 2 , R 21 , R 3 and G are defined herein. Pharmaceutical compositions containing the compounds and methods of using the compounds are also disclosed.

  本发明的化合物，例如公式IIa、IIb、IIc或IId的化合物，以及其药学上可接受的盐、异构体和前药，可用作肝X受体活性调节剂，其中R1、R2、R21、R3和G在此定义。还公开了含有这些化合物的药物组合物和使用这些化合物的方法。
• NHC-Catalyzed Enantioselective [3 + 3] Annulation to Construct 5,6-Dihydropyrimidin-4-ones
  作者：Di Meng、Yangxi Xie、Qiupeng Peng、Jian Wang

  DOI：10.1021/acs.orglett.0c02832

  日期：2020.10.2

  The unprecedented enantioselective NHC-catalyzed [3 + 3] annulation of alpha-bromoenals with amidines via a dual C-N bond formation is described. The protocol allows a rapid preparation of 5,6-dihydropyrimidinones in acceptable yields with good enantioselectivities.
• Investigating Scale-Up and Further Applications of DABAL-Me₃ Promoted Amide Synthesis
  作者：Darren S. Lee、Zacharias Amara、Martyn Poliakoff、Thomas Harman、Gary Reid、Barrie Rhodes、Steve Brough、Thomas McInally、Simon Woodward

  DOI：10.1021/acs.oprd.5b00101

  日期：2015.7.17

  Methods for the batch scale up of DABAL-Me-3 promoted direct ester to amide synthesis have been demonstrated at 10-100 g scales using a tert-amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me-3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h(-1)). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me-3, resulting in the clean formation of free amidines (16 examples) and amidrazones.
• Base-promoted formal [4 + 1+1] annulation of aldehyde, N -benzyl amidine and DMSO toward 2,4,6-triaryl pyrimidines
  作者：Jin Yuan、Jingbo Li、Bingbing Wang、Song Sun、Jiang Cheng

  DOI：10.1016/j.tetlet.2017.11.020

  日期：2017.12

  A base-promoted formal [4 + 1+1] annulation of aldehyde, N-benzyl amidine and DMSO was developed, leading to a series of 2,4,6-triaryl pyrimidines in moderate to good yields. Notably, DMSO served as a methine source, which was activated by base rather than either Lewis acid or electrophile. Molecular O-2 was the sole eco-friendly oxidant during this procedure. (C) 2017 Published by Elsevier Ltd.